Nalorphine
Nalorphine is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties. It was introduced in 1954 and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence.
Nalorphine was the second opioid antagonist to be introduced, preceded by nalodeine in 1915 and followed by naloxone in 1960 and naltrexone in 1963. Due to potent activation of the κ-opioid receptor, nalorphine produces side effects such as dysphoria, anxiety, confusion, and hallucinations, and for this reason, is no longer used medically.Pharmacology
Pharmacodynamics
Nalorphine acts at two opioid receptors — the μ-opioid receptor where it has antagonistic effects, and at the κ-opioid receptor where it exerts high-efficacy partial agonist/near-full agonist characteristics.Chemistry
Analogues
Nalorphine has a number of analogues including niconalorphine, diacetylnalorphine, dihydronalorphine, and a number of others as well as a number of codeine-based analogues.Synthesis
More recently, it has become much more commonplace to use ethyl chloroformate instead of cyanogen bromide for the Von Braun degradation demethylation step. See for example the list of phenyltropanes or the synthesis of paroxetine for further examples of this.